Supplementary Material. Photostimulated synthesis of 2-(diphenylphosphino)benzoic acid by the S RN 1 reaction

Size: px
Start display at page:

Download "Supplementary Material. Photostimulated synthesis of 2-(diphenylphosphino)benzoic acid by the S RN 1 reaction"

Transcription

1 Supplementary Material Photostimulated synthesis of 2-(diphenylphosphino)benzoic acid by the S RN 1 reaction Silvia M. Barolo, Sandra E. Martín,* Roberto A. Rossi* INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba, 5000, Argentina rossi@fcq.unc.edu.ar Table of Contents Results and Discussion of Annex Material S2 Experimental Section S3 General S3 Materials S3 Representative Procedure for Photostimulated Reactions in Liquid Ammonia S3 1 H NMR spectrum of Ethyl 2-(diphenylphosphoryl)benzoate (4) S5-S7 13 C NMR spectrum of Ethyl 2-(diphenylphosphoryl)benzoate (4) S8-S9 31 P NMR spectrum of Ethyl 2-(diphenylphosphoryl)benzoate (4) S10 1 H-NMRspectrum of Ethyl benzoate (5) S11-S12 13 C-NMR spectrum of Ethyl benzoate (5) S13-S14 1 H-NMR spectrum of Ethyl 2-chlorobenzoate (6) S15-S16 13 C-NMR spectrum of Ethyl 2-chlorobenzoate (6) S17-S18 MS of Ethyl benzoate (5) and Ethyl 2-chlorobenzoate (6) S19 Page S1

2 Results and Discussion of Annex Material To extend the studies, we conducted news experiments in liquid ammonia at -78 ºC with 1 equiv. of 1, 1 equiv. of Ph 2 P ions and 2.5 h of stirring before adding 2-chlorobenzoate ion (1), as those previously reported. 1 However, the reactions were carried out in a photochemical reactor equipped with two metal iodide lamps of 400 W (Philips, Model HPI-T, water refrigerated), and quenched by adding NH 4 NO 3 in excess instead of adding THF at 30 min of reaction. Typically, product analyses were conducted by esterification of the phosphine to the corresponding esters (ethyl 2-(diphenylphosphoryl)benzoate (4), ethyl benzoate (5) and ethyl 2-chlorobenzoate (6)) with ensuing determination by GC. Results are summarized in Table S1. When the photostimulated reaction of 1 with Ph 2 P ions was carried out in this condition, the substitution product was obtained only in 11% yield and 75% of the substrate remained unaltered (entry 1, Table S1). The reaction did not occur in the dark (entry 2, Table S1). In addition, the photostimulated reactions were also inhibited by small amounts of electron acceptors (m-dnb) or free-radical traps (TEMPO) (entries 3 and 4, Table S1). Once again, all these results suggets that the reaction proceeds through the S RN 1 mechanism. In adition, we shows that without quenched by adding NH 4 NO 3 in excess, the reaction continue to progress beyond the addition of THF, during the time of solvent evaporation and consequente increase in temperature (-78 to -33 ºC) (compare entry 1, Table 2 with entry 1, Table S1). Table S1. Reactions of 1 with Ph 2 P ions under the experimental conditions reported in ref. 1 and quenched with NH 4 NO 3 Entry Conditions a Cl - (%) b 4 (%) c 6 (%) c 5 (%) c 1 NH 3, -78ºC, hv, 30 min >5 2 d NH 3, -78ºC, dark, 30 min >1 -- ca e NH 3, -78ºC, hv, 30 min >1 -- ca f NH 3, -78ºC, hv, 30 min >1 -- ca a Reactions carried out under N 2 in ml of ammonia at -78ºC, with 1 equiv. (4.44 mmoles) of 1, 1 equiv. (4.44 mmoles) of Ph 2 P ions and 2.5 h of stirring before adding 1 and 0.5 h of stirring before adding of an excess of NH 4 NO 3. Is important to note that t-buoh was not added. Irradiation was conducted in a photochemical reactor equipped with two 400 W lamps refrigerated with air and water unless otherwise indicated. b Determined potentiometrically. c Yields were determined by GC (internal standard method). d 2-Chlorobenzoic acid was added in one portion. e 20 mol % of m-dnb was added. f 20 mol % of TEMPO was added. Page S2

3 Experimental Section General. Gas chromatographic analyses were performed on a Hewlett Packard 5890 series II with a flame ionization detector and equipped with the following column: HP1 column (0.53 mm x 5m). Quantification by GC was performed by the internal standard method. Gas Chromatographic-Mass Spectrometer analyses were carried out on a Shimadzu QP-5050 spectrometer equipped with a quadrupole detector and a VF-5 ms column (30 m x 0.25 mm x 0.25 μm). 1 H NMR ( MHz), 31 P NMR (162 MHz) and 13 C NMR ( MHz) spectra were recorded on a High Resolution Spectrometer Bruker Advance 400 in CDCl 3 as solvent and against internal TMS ( 1 H) and external 85% phosphoric acid ( 31 P). Coupling constants (J) are given in Hz units. Irradiation was conducted in a reactor equipped with two 400-W lamps of metal iodide (Philips, Model HPI-T) refrigerated with water. An Orion 420A phmeter with Ag/Ag + electrode was used for the potentiometric titration of halide ions in the aqueous phases. Materials C 6 H 5 CO 2 H, 2-ClC 6 H 4 CO 2 H, Na metal, Ph 3 P, t-buoh, NH 4 NO 3, EtOH and H 2 SO 4 were commercially available and used as received from the supplier. THF was dried over Na metal and benzophenone, and distilled under atmosphere of N 2. All solvents were analytical grade and used as received from the supplier. Silica gel ( mm Macherey-Nagel) was used in column chromatography. Ethyl benzoate and ethyl 2- chlorobenzoate were prepared according to the literature procedure. 2 Representative Procedure for Photostimulated Reactions of 1 with Ph 2 P ions in Liquid Ammonia Liquid ammonia (150 ml), previously dried with Na metal under N 2, was condensed into a 250 ml three-necked, round-bottomed flask equipped with a coldfinger condenser charged with ethanol, a nitrogen inlet, and a magnetic stirrer. PPh 3 ( g, 0.55 mmol) was then added, and Na metal was introduced in small pieces; addition was continued until the solution kept its dark brown color for at least 15 min. After its color turned red, t-buoh (0.5 ml, 0.55 mmol) was added to eliminate the H 2 N anions formed. An orange solution of Ph 2 P ions was obtained. 2- Chlorobenzoic acid was added to the solution to form 1 ( g, 0.5 mmol), and the mixture was irradiated for 120 min with two metal iodide lamps of 400 W (Philips, Model HPI-T, water refrigerated). The reaction was quenched with an excess of NH 4 NO 3 and the liquid ammonia was allowed to evaporate. Water (50 ml) was added to the residue and HCl was afterwards added until the aqueous phase reached ph 1-2. The Page S3

4 aqueous phase was extrated with ethyl acetate (3 x 30 ml) and the combined organic layers were washed with H 2 O (20 ml) and dried over anhydrous MgSO 4; the solvent was evaporated under vacuum. The chloride ions in the aqueous solution were determined by potentiometry. The crude products were mixed with EtOH (1.8 ml, 30.8 mmol) and concentrate H 2 SO 4 (0.05 ml, 0.94 mmol) in a 10 ml tube sealed and equipped with a magnetic stirrer. The mixture was heated to 80 C for 4 days. The excess of EtOH was eliminated on a rotary evaporator and allowed cooling. The residue was dissolved with water (50 ml) and NaHCO 3 was then added until have ph 8-9. The aqueous phase was extracted with ethyl acetate (3 x 30 ml) and the combined organic layers were washed with H 2 O (20 ml), dried over anhydrous MgSO 4 and then quantified by GC using the internal standard method. Alternatively, in other runs the solvent was removed under reduced pressure and the product ethyl 2-(diphenylphosphoryl)benzoate (4) 3 was purified by column chromatography on silica gel eluting with a dichloromethane / etanol gradient (100:0 95:5) as a colourless liquid. 1 H NMR ( MHz, CDCl 3 ): H (1H aro, m, 1CH), (13 H aro, m, 13CH), 3.97 (2H, q, J HH = 7.2 Hz, CH 2 CH 3 ), 1.00 (3H, t, J HH = 7.2 Hz, CH 2 CH 3 ). 13 C NMR ( MHz, CDCl 3 ): C (d, J = 3 Hz), (d, J = 6 Hz), (d, J = 10 Hz), (d, J = 108 Hz), (d, J = 99 Hz), (d, J = 10 Hz), (d, J = 3 Hz), (d, J = 12 Hz), (d, J = 8 Hz), (d, J = 13 Hz), (s, CH 2 CH 3 ), (s, CH 2 CH 3 ). 31 P NMR (162 MHz, CDCl 3 ): P MS, m/z (%) = 350 (M +, 2), 349 (4), 322 (30), 321 (88), 305 (21), 303 (25), 278 (11), 277 (35), 274 (20), 273 (100), 257 (16), 246 (17), 245 (87), 229 (25), 228 (13), 227 (31), 201 (15), 200 (16), 199 (35), 183 (12), 168 (11), 167 (22), 153 (17), 152 (51), 105 (12), 77 (56), 51(20). ESI-HRMS Anal. Calcd for C 21 H 19 O 3 PNa + (M+ Na + ) , found References 1. Kemme, S. T.; Schmidt, Y.; Grünanger, C. U.; Laungani, A. C.; Herber, C.; Breit, B. Synthesis 2010, Furniss, B. S.; Hannaford, A. J.; Smith P. W. G.; Tatchell, A. R. Vogel s Textbook of Practical Organic Chemistry, 5th Edn., Addison-Wesley, 1989, pp Crich, D.; Dyker, H. Tetrahedron Lett. 1989, 30, 475. Page S4

5 ppm Page S5

6 ppm Page S6

7 ppm ppm Page S7

8 ppm Page S8

9 ppm ppm Page S9

10 ppm Page S10

11 ppm Page S11

12 ppm Page S12

13 ppm Page S13

14 ppm Page S14

15 ppm Page S15

16 ppm Page S16

17 Page 100 S ppm ARKAT-USA, Inc

18 ppm Page S18

19 Ethyl benzoate (5). MS: m/z (%) = 151 (2); 150 (19); 122 (28); 106 (9); 105 (100); 84 (7); 78 (6); 77 (49); 76 (6); 51 (28); 50 (9); 49 (7). Ethyl 2-chlorobenzoate (6). MS: m/z (%) =185 (3); 184 (12); 158 (8); 156 (26); 141 (31); 140 (10); 139 (100); 113 (10); 111 (27); 76 (10); 75 (31); 74 (7); 51 (7); 50 (16); 49 (7). Page S19

Supporting Information

Supporting Information Supporting Information An Extremely Active and General Catalyst for Suzuki Coupling Reactions of Unreactive Aryl Chlorides Dong-Hwan Lee and Myung-Jong Jin* School of Chemical Science and Engineering,

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Rh 2 (Ac) 4 -Catalyzed 2,3-Migration of -rrocenecarboxyl -Diazocarbonyl

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic

More information

Supporting Information

Supporting Information Supporting Information An efficient and general method for the Heck and Buchwald- Hartwig coupling reactions of aryl chlorides Dong-Hwan Lee, Abu Taher, Shahin Hossain and Myung-Jong Jin* Department of

More information

Supporting Information

Supporting Information Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,

More information

Supplementary Information

Supplementary Information Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)

More information

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi

More information

Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts by Co-Polymerisation

Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts by Co-Polymerisation Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts

More information

N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides

N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Electronic supplementary information for -Hydroxyphthalimide: a new photoredox catalyst for [4+1]

More information

A biphasic oxidation of alcohols to aldehydes and ketones using a simplified packed-bed microreactor

A biphasic oxidation of alcohols to aldehydes and ketones using a simplified packed-bed microreactor A biphasic oxidation of alcohols to aldehydes and ketones using a simplified packed-bed microreactor Andrew Bogdan 1 and D. Tyler McQuade 2, * Address: 1 Department of Chemistry and Chemical Biology, Cornell

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information General and highly active catalyst for mono and double Hiyama coupling reactions of unreactive aryl chlorides in water Dong-Hwan Lee, Ji-Young Jung, and Myung-Jong

More information

How to build and race a fast nanocar Synthesis Information

How to build and race a fast nanocar Synthesis Information How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz,

More information

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated

More information

Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins

Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins S1 Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins Antonia Kouridaki, Tamsyn Montagnon, Maria Tofi and Georgios Vassilikogiannakis* Department of

More information

Electronic Supplementary Material

Electronic Supplementary Material Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly

More information

4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester

4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester NP 4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester NaEt C 10 H 18 4 Na C 2 H 6 C 8 H 12 3 (202.2) (23.0) (46.1) (156.2) Classification Reaction types and substance

More information

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,

More information

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS

More information

Electronic Supplementary Information (ESI)

Electronic Supplementary Information (ESI) Electronic Supplementary Information (ESI) A thin-layered chromatography plate prepared from naphthalimide-based receptor immobilized SiO 2 nanoparticles as a portable chemosensor and adsorbent for Pb

More information

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone

More information

Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain

Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry

More information

SYNTHESIS OF A 3-THIOMANNOSIDE

SYNTHESIS OF A 3-THIOMANNOSIDE Supporting Information SYNTHESIS OF A 3-THIOMANNOSIDE María B Comba, Alejandra G Suárez, Ariel M Sarotti, María I Mangione* and Rolando A Spanevello and Enrique D V Giordano Instituto de Química Rosario,

More information

Photostimulated synthesis of 2-(diphenylphosphino)benzoic acid by the S RN 1 reaction

Photostimulated synthesis of 2-(diphenylphosphino)benzoic acid by the S RN 1 reaction Photostimulated synthesis of 2-(diphenylphosphino)benzoic acid by the S RN 1 reaction Silvia M. Barolo, Sandra E. Martín,* and Roberto A. Rossi* INFIQC, Departamento de Química Orgánica, Facultad de Ciencias

More information

Kinetics experiments were carried out at ambient temperature (24 o -26 o C) on a 250 MHz Bruker

Kinetics experiments were carried out at ambient temperature (24 o -26 o C) on a 250 MHz Bruker Experimental Materials and Methods. All 31 P NMR and 1 H NMR spectra were recorded on 250 MHz Bruker or DRX 500 MHz instruments. All 31 P NMR spectra were acquired using broadband gated decoupling. 31

More information

Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy

Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted

More information

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL

More information

Supporting Information. Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones

Supporting Information. Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones Supporting Information Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones Marco Bandini,* Riccardo Sinisi, Achille Umani-Ronchi* Dipartimento di Chimica Organica G. Ciamician, Università

More information

Synthesis and nucleophilic aromatic substitution of 3- fluoro-5-nitro-1-(pentafluorosulfanyl)benzene

Synthesis and nucleophilic aromatic substitution of 3- fluoro-5-nitro-1-(pentafluorosulfanyl)benzene Supporting Information for Synthesis and nucleophilic aromatic substitution of 3- fluoro-5-nitro-1-(pentafluorosulfanyl)benzene Javier Ajenjo 1, Martin Greenhall 2, Camillo Zarantonello 2 and Petr Beier

More information

Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis

Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Kazushi Watanabe, Yuto Suzuki, Kenta Aoki, Akira Sakakura, Kiyotake Suenaga, and Hideo Kigoshi* Department of Chemistry,

More information

Enantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex

Enantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supplementary Information Enantioselectivity switch in copper-catalyzed conjugate addition

More information

dichloropyrimidine (1.5 g, 10.1 mmol) in THF (10 ml) added at -116 C under nitrogen atmosphere.

dichloropyrimidine (1.5 g, 10.1 mmol) in THF (10 ml) added at -116 C under nitrogen atmosphere. Supporting Information Experimental The presence of atropisomerism arising from diastereoisomerism is indicated in the 13 C spectra of the relevant compounds with the second isomer being indicated with

More information

Supplementary Material. Ionic liquid iodinating reagent for mild and efficient iodination of. aromatic and heteroaromatic amines and terminal alkynes

Supplementary Material. Ionic liquid iodinating reagent for mild and efficient iodination of. aromatic and heteroaromatic amines and terminal alkynes Supplementary Material onic liquid iodinating reagent for mild and efficient iodination of aromatic and heteroaromatic amines and terminal alkynes Mahboobe Nouzarian 1, Rahman Hosseinzadeh 1,*, and Hamid

More information

Supplementary Information

Supplementary Information Supplementary Information J. Braz. Chem. Soc., Vol. 26, No. 4, S1-S16, 2015. Printed in Brazil - 2015 Sociedade Brasileira de Química 0103-5053 $6.00+0.00 SI Jaqueline P. Vargas, a Lucimar M. Pinto, b

More information

2017 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide

2017 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide 217 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide O O Cl NH 3 NH 2 C 9 H 7 ClO (166.6) (17.) C 9 H 9 NO (147.2) Classification Reaction types and substance classes reaction of

More information

Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media

Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous

More information

Supplementary Material

Supplementary Material Supplementary Material Rongalite /PEG 400 as reducing system in the synthesis of new glycerol derived selenol esters using anhydrides and bis (2,2 dimethyl 1,3 dioxolanylmethyl)diselenide as substrates

More information

Synthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity

Synthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity Supporting Information for Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity Jinghan Gui,* Hailong Tian, and Weisheng Tian* Key Laboratory of Synthetic

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003 Supporting Information for Angew. Chem. Int. Ed. Z53001 Wiley-VCH 2003 69451 Weinheim, Germany 1 Ordered Self-Assembly and Electronic Behavior of C 60 -Anthrylphenylacetylene Hybrid ** Seok Ho Kang 1,

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 214 Supporting Information Rapid and sensitive detection of acrylic acid using a novel fluorescence

More information

Aminoacid Based Chiral N-Amidothioureas. Acetate Anion. Binding Induced Chirality Transfer

Aminoacid Based Chiral N-Amidothioureas. Acetate Anion. Binding Induced Chirality Transfer Aminoacid Based Chiral -Amidothioureas. Acetate Anion Binding Induced Chirality Transfer Fang Wang, a Wen-Bin He, a Jin-He Wang, a Xiao-Sheng Yan, a Ying Zhan, a Ying-Ying Ma, b Li-Cai Ye, a Rui Yang,

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Micro- and mesoporous poly(schiff-base)s

More information

Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol

Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol S1 Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2010 Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol Julien

More information

Figure S1 - Enzymatic titration of HNE and GS-HNE.

Figure S1 - Enzymatic titration of HNE and GS-HNE. Figure S1 - Enzymatic titration of HNE and GS-HNE. Solutions of HNE and GS-HNE were titrated through their reduction to the corresponding alchools catalyzed by AR, monitoring the decrease in absorbance

More information

A TTFV pyrene-based copolymer: synthesis, redox properties, and aggregation behaviour

A TTFV pyrene-based copolymer: synthesis, redox properties, and aggregation behaviour Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 A TTFV pyrene-based copolymer: synthesis, redox properties, and aggregation behaviour Eyad

More information

Efficient Pd-Catalyzed Amination of Heteroaryl Halides

Efficient Pd-Catalyzed Amination of Heteroaryl Halides 1 Efficient Pd-Catalyzed Amination of Heteroaryl Halides Mark D. Charles, Philip Schultz, Stephen L. Buchwald* Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 Supporting

More information

SUPPORTING INFORMATION

SUPPORTING INFORMATION SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry

More information

Supporting Information

Supporting Information Supporting Information Precision Synthesis of Poly(-hexylpyrrole) and its Diblock Copolymer with Poly(p-phenylene) via Catalyst-Transfer Polycondensation Akihiro Yokoyama, Akira Kato, Ryo Miyakoshi, and

More information

Supporting Information

Supporting Information Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook

More information

Block: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection

Block: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection Electronic Supplementary Information (ESI) Luminogenic Materials Constructed from Tetraphenylethene Building Block: Synthesis, Aggregation-Induced Emission, Two-Photon Absorption, Light Refraction, and

More information

Synthesis of Dihydroquinoline Based Merocyanines as Naked Eye and Fluorogenic sensors for Hydrazine Hydrate in Aqueous Medium

Synthesis of Dihydroquinoline Based Merocyanines as Naked Eye and Fluorogenic sensors for Hydrazine Hydrate in Aqueous Medium Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Synthesis of Dihydroquinoline Based Merocyanines as Naked Eye and Fluorogenic sensors for Hydrazine

More information

Supporting Information. Rhodium, iridium and nickel complexes with a. 1,3,5-triphenylbenzene tris-mic ligand. Study of

Supporting Information. Rhodium, iridium and nickel complexes with a. 1,3,5-triphenylbenzene tris-mic ligand. Study of Supporting Information for Rhodium, iridium and nickel complexes with a 1,3,5-triphenylbenzene tris-mic ligand. Study of the electronic properties and catalytic activities Carmen Mejuto 1, Beatriz Royo

More information

Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4)

Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) A solution of propenyl magnesium bromide in THF (17.5 mmol) under nitrogen atmosphere was cooled in an ice bath and

More information

Supporting Information for

Supporting Information for Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,

More information

Supplementary Information

Supplementary Information Supplementary Information Supramolecular polymerization of hydrogen-bonded rosettes with anthracene chromophores: regioisomeric effect on nanostructures Deepak D. Prabhu, Keisuke Aratsu, Mitsuaki Yamauchi,

More information

Fluorescent Chemosensor for Selective Detection of Ag + in an. Aqueous Medium

Fluorescent Chemosensor for Selective Detection of Ag + in an. Aqueous Medium Electronic supplementary information For A Heptamethine cyanine -Based Colorimetric and Ratiometric Fluorescent Chemosensor for Selective Detection of Ag + in an Aqueous Medium Hong Zheng *, Min Yan, Xiao-Xing

More information

Supporting Information for

Supporting Information for Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for

More information

Synthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition

Synthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition Synthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition Sonia Amel Diab, Antje Hienzch, Cyril Lebargy, Stéphante Guillarme, Emmanuel fund

More information

Supplementary Information. Rational Design of Soluble and Clickable Polymers Prepared by. Conventional Free Radical Polymerization of

Supplementary Information. Rational Design of Soluble and Clickable Polymers Prepared by. Conventional Free Radical Polymerization of Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2017 Supplementary Information Rational Design of Soluble and Clickable Polymers Prepared by

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Negishi reaction in BODIPY dyes. Unprecedented alkylation by palladium-catalyzed

More information

Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle

Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Supporting Information Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Liu-Pan Yang, a,b Fei Jia, a Jie-Shun Cui, a Song-Bo Lu, a and Wei Jiang* a a Department of Chemistry, South

More information

Supporting Information: Regioselective esterification of vicinal diols on monosaccharide derivatives via

Supporting Information: Regioselective esterification of vicinal diols on monosaccharide derivatives via Supporting Information: Regioselective esterification of vicinal diols on monosaccharide derivatives via Mitsunobu reactions. Guijun Wang,*Jean Rene Ella-Menye, Michael St. Martin, Hao Yang, Kristopher

More information

Rational design of light-directed dynamic spheres

Rational design of light-directed dynamic spheres Electronic Supplementary Information (ESI) Rational design of light-directed dynamic spheres Yumi Okui a and Mina Han* a,b a Department of Chemistry and Department of Electronic Chemistry Tokyo Institute

More information

Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol.

Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol. Tetrahedron Letters 1 Pergamon TETRAHEDRN LETTERS Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol. Jennifer L. Stockdill,

More information

Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes

Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,

More information

Supplementary Information

Supplementary Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supplementary Information SUPPORTING INFORMATION Novel and selective detection of Tabun mimics

More information

A colorimetric and fluorescent turn-on sensor for pyrophosphate. anion based on dicyanomethylene-4h-chromene framework

A colorimetric and fluorescent turn-on sensor for pyrophosphate. anion based on dicyanomethylene-4h-chromene framework Electronic Supplementary Information (ESI) A colorimetric and fluorescent turn-on sensor for pyrophosphate anion based on dicyanomethylene-4h-chromene framework Xiaomei Huang, Zhiqian Guo, Weihong Zhu*,

More information

A Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones. Jin-Quan Yu, a and E. J.

A Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones. Jin-Quan Yu, a and E. J. A Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones Jin-Quan Yu, a and E. J. Corey b * a Department of Chemistry, Cambridge University, Cambridge CB2 1EW, United

More information

Electronic Supporting Information

Electronic Supporting Information Electronic Supporting Information Reactions of Tp(NH=CPh 2 )(PPh 3 )Ru Cl with HC CPh in the presence of H 2 O: Insertion/Hydration Products Chih-Jen Cheng, a Hung-Chun Tong, a Yih-Hsing Lo,* b Po-Yo Wang,

More information

Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions

Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions SUPPORTIG IFORMATIO Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions Alexey Volkov, a Fredrik Tinnis, a and Hans Adolfsson.* a a Department of Organic Chemistry,

More information

A fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media

A fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media Supplementary Information A fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media Weiwei Wang and Quanrui Wang* Department of Chemistry,

More information

Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and

Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and Supporting Information for A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3- butyn-2-ols Jie Li and

More information

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Supporting Material 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Srinivas Olepu a, Praveen Kumar Suryadevara a, Kasey Rivas b, Christophe L. M. J. Verlinde

More information

Supporting Information

Supporting Information Supporting Information for Dual-stimuli responsive fluorescent supramolecular polymer based on a diselenium-bridged pillar[5]arene dimer and an AIE-active tetraphenylethylene guest Yan Wang, Ming-Zhe Lv,

More information

A dual-model and on off fluorescent Al 3+ /Cu 2+ - chemosensor and the detection of F /Al 3+ with in situ prepared Al 3+ /Cu 2+ complex

A dual-model and on off fluorescent Al 3+ /Cu 2+ - chemosensor and the detection of F /Al 3+ with in situ prepared Al 3+ /Cu 2+ complex Supporting Information (SI) A dual-model and on off fluorescent Al 3+ /Cu 2+ - chemosensor and the detection of F /Al 3+ with in situ prepared Al 3+ /Cu 2+ complex Xiaoya Li, Mingming Yu, Faliu Yang, Xingjiang

More information

Accessory Information

Accessory Information Accessory Information Synthesis of 5-phenyl 2-Functionalized Pyrroles by amino Heck and tandem amino Heck Carbonylation reactions Shazia Zaman, *A,B Mitsuru Kitamura B, C and Andrew D. Abell A *A Department

More information

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in Supplementary Figure 1. Optical properties of 1 in various solvents. UV/Vis (left axis) and fluorescence spectra (right axis, ex = 420 nm) of 1 in hexane (blue lines), toluene (green lines), THF (yellow

More information

Department of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures

Department of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures Supporting Information Low Temperature n-butyllithium-induced [3,3]-Sigmatropic Rearrangement/Electrophile Trapping Reactions of Allyl-1,1- Dichlorovinyl Ethers. Synthesis of - - and -lactones. Aaron Christopher

More information

Synthesis of Levulinic Acid based Poly(amine-co-ester)s

Synthesis of Levulinic Acid based Poly(amine-co-ester)s Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2018 Synthesis of Levulinic Acid based Poly(amine-co-ester)s Yann Bernhard, Lucas Pagies, Sylvain

More information

A General and Mild Copper-Catalyzed Arylation of Diethyl Malonate

A General and Mild Copper-Catalyzed Arylation of Diethyl Malonate A General and Mild Copper-Catalyzed Arylation of Diethyl Malonate 1 Edward J. Hennessy and Stephen L. Buchwald Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 Supporting

More information

Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry Supplementary data

Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry Supplementary data Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2012 Supplementary data Cu-catalyzed in situ generation of thiol using xanthate as thiol

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2012 69451 Weinheim, Germany Concise Syntheses of Insect Pheromones Using Z-Selective Cross Metathesis** Myles B. Herbert, Vanessa M. Marx, Richard L. Pederson, and Robert

More information

The all-photochemical Synthesis an. OGP (10-14) Precursor

The all-photochemical Synthesis an. OGP (10-14) Precursor SUPPORTING INFORMATION The all-photochemical Synthesis an OGP (10-14) Precursor Jean-Luc Débieux, Christian G. Bochet* Department of Chemistry, University of Fribourg, 9 Chemin du Musée, CH-1700 Fribourg,

More information

Supplementary Material

Supplementary Material 10.1071/CH13324_AC CSIRO 2013 Australian Journal of Chemistry 2013, 66(12), 1570-1575 Supplementary Material A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination

More information

Supporting Information

Supporting Information Supporting Information Visible Light-Induced External Oxidant-Free Oxidative Phosphonylation of C(sp 2 )-H Bonds Linbin Niu, 1 Jiamei Liu, 1 Hong Yi, 1 Shengchun Wang, 1 Xing-An Liang, 1 Atul K. Singh,

More information

with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15

with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15 2. A solution of Rhodamine B (14.2 g, 30.0 mmol) in CH 2 Cl 2 (40 ml) was treated with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15 g, 30.0 mmol) and TEA (4.21 ml, 3.03 g, 30.0

More information

BODIPY Based Self-healing Fluorescent Gel Formation via Acylhydrazone Linkage

BODIPY Based Self-healing Fluorescent Gel Formation via Acylhydrazone Linkage Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 BODIPY Based Self-healing Fluorescent Gel Formation via Acylhydrazone Linkage Tugba Ozdemir

More information

Sensitive and reliable detection of glass transition of polymers. by fluorescent probes based on AIE luminogens

Sensitive and reliable detection of glass transition of polymers. by fluorescent probes based on AIE luminogens Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting information Sensitive and reliable detection of glass transition of polymers

More information

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 S1 Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 David Bézier, Sehoon Park and Maurice Brookhart* Department of Chemistry, University of North Carolina at Chapel Hill,

More information

A thermally remendable epoxy resin

A thermally remendable epoxy resin Supplementary Information A thermally remendable epoxy resin Qiao Tian a, Yan Chao Yuan a, Min Zhi Rong *b, Ming Qiu Zhang b a Key Laboratory for Polymeric Composite and Functional Materials of Ministry

More information

Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12

Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12 Supporting Information Table of Contents page 1. General Notes 2 2. Experimental Details 3-12 3. NMR Support for Timing of Claisen/Diels-Alder/Claisen 13 4. 1 H and 13 C NMR 14-37 General Notes All reagents

More information

Supporting Information

Supporting Information Supporting Information Divergent Reactivity of gem-difluoro-enolates towards Nitrogen Electrophiles: Unorthodox Nitroso Aldol Reaction for Rapid Synthesis of -Ketoamides Mallu Kesava Reddy, Isai Ramakrishna,

More information

Production of Renewable 1,3-Pentadiene from Xylitol via Formic. Acid-Mediated Deoxydehydration and Palladium-Catalyzed

Production of Renewable 1,3-Pentadiene from Xylitol via Formic. Acid-Mediated Deoxydehydration and Palladium-Catalyzed Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2016 Production of Renewable 1,3-Pentadiene from Xylitol via Formic Acid-Mediated Deoxydehydration

More information

Efficient Synthesis of Macrocyclic Ketones Via Palladium-Catalyzed Activation of Carboxylic Acids

Efficient Synthesis of Macrocyclic Ketones Via Palladium-Catalyzed Activation of Carboxylic Acids ELECTRONIC SUPPORTING INFORMATION Efficient Synthesis of Macrocyclic Ketones Via Palladium-Catalyzed Activation of Carboxylic Acids Anant R. Kapdi, a,b * and Ian J. S. Fairlamb a, * a Department of Chemistry,

More information

5.37 Introduction to Organic Synthesis Laboratory

5.37 Introduction to Organic Synthesis Laboratory MIT pencourseware http://ocw.mit.edu 5.37 Introduction to rganic Synthesis Laboratory Spring 2009 For information about citing these materials or our Terms of Use, visit: http://ocw.mit.edu/terms. URIECA

More information

Supporting Information

Supporting Information Supporting Information Efficient Short Step Synthesis of Corey s Tamiflu Intermediate Nsiama Tienabe Kipassa, Hiroaki kamura, * Kengo Kina, Tetsuo Iwagawa, and Toshiyuki Hamada Department of Chemistry

More information

A Sumanene-based Aryne, Sumanyne

A Sumanene-based Aryne, Sumanyne A Sumanene-based Aryne, Sumanyne Niti Ngamsomprasert, Yumi Yakiyama, and Hidehiro Sakurai* Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871

More information

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A Fuerst et al. Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A S1 Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers:

More information

Significant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes

Significant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes Significant improvement of dye-sensitized solar cell performance by a slim phenothiazine based dyes Yong Hua, a Shuai Chang, b Dandan Huang, c Xuan Zhou, a Xunjin Zhu, *a,d Jianzhang Zhao, c Tao Chen,

More information

Synthesis of borinic acids and borinate adducts using diisopropylaminoborane

Synthesis of borinic acids and borinate adducts using diisopropylaminoborane Synthesis of borinic acids and borinate adducts using diisopropylaminoborane Ludovic Marciasini, Bastien Cacciuttolo, Michel Vaultier and Mathieu Pucheault* Institut des Sciences Moléculaires, UMR 5255,

More information

Halogen halogen interactions in diiodo-xylenes

Halogen halogen interactions in diiodo-xylenes Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society

More information